Vanillin → 24033-07-6

HRID 1603738Notes

Reaction equation

HRID 1603738 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[OH:11])[CH:6]=O.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=1.CCOCC>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[OH:11])[CH:6]=[N:20][C:17]1[CH:18]=[CH:19][C:14]([O:13][CH3:12])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 1183VanillinHCID 3283Diethyl EtherHCID 7732P-Anisidine

Product 1

HCID 68137024033-07-6

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

3-Methoxy-4-hydroxybenzaldehyde (vanillin, 1 g, 6.57 mmol) was dissolved in methanol (30 ml). To this solution was added p-anisidine (0.810 g, 6.57 mmol) and the resultant reaction solution was stirred overnight under nitrogen at room temperature. The reaction solution was taken to dryness in vacuo with the application of heat. The resultant solid was azeotropically mixed with methanol (2×), ether (1×), and again with methanol (2×) to yield yellow crystals. The crystals were triturated with hot ether to yield the title product: 1H NMR (300 MHz, CDCl3); δ 8.36 (S, 1H) 7.60 (S, 1H), 7.30-7.17 (m, 3H), 7.05-6,91 (m, 3H), 6.10 (S, 1H), 3.97 (S, 3H), 3.83 (S, 3H)

Workup

  1. customthe resultant reaction solution
  2. temperatureof heat
  3. customThe crystals were triturated with hot ether

Sources & evidence

ORD record
ord-dfaa366960c7496589cabb2b01575717
Source dataset
uspto-grants-1999_11
Patent number
US05990137

Reaction notes

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